Compounds useful as anti-inflammatory agents which are aromatic compounds, especially substituted tert-butylphenol compounds, and related derivatives thereof, with an aliphatic ketone substituent having a terminally unsaturated moiety are disclosed in U.S. Pat. No. 4,708,966, issued to Loomans, Matthews & Miller on Nov. 24, 1987; and in copending patent applications entitled "Cyclic Anti-Inflammatory Derivatives of Di-tert-butylphenol Compounds" of Dobson, Loomans, Matthews & Miller, Ser. No. 123,756, and "Tert-Butyl Phenyl Compounds Useful as Anti-Inflammatory Agents of Loomans, Matthews & Miller, Ser. No. 123,694, both filed on Nov. 23, 1987.
Friedel-Crafts reactions of aromatic hydrocarbons with acyl halides in the presence of a catalyst such as anhydrous aluminum chloride to produce aromatic compounds having an aliphatic ketone substituent are well-known. However, when the acyl halide reactant has a labile portion, such as a terminally unsaturated moiety, many unwanted side reactions can occur, such that the yield of the desired product is low. This has made preparation of certain substituted aromatic compounds, with an aliphatic ketone substituent having a labile moiety, in large quantities and with good yields a difficult task.
It is an object of the present invention to provide a process for the preparation of aromatic compounds, with an aliphatic ketone substituent having a labile portion.
It is a further object of the present invention to provide a process for the preparation of such compounds from aromatic and acyl halide reactants with good yield.